So I've been reading your blog for a while, and thinking about the questions you ask there for even longer. I don't have any answers for you, sorry.
I do have the gnawing fear, from time to time, that the entire universe is the exact size and shape of the inside of my skull. Thinking about existence and meaning and purpose is all I can do about it, but I haven't found it particularly helpful because then I'm just employing my mind to explore my mind, and knowing the floorplan of the prison isn't the same as being free.
I'd like to say that connections like those you mention on your blog offer a path out of ourselves, and maybe they do, for a moment. So do literature and cinema and booze and fornicating and improv. And, yeah, advertising. They're all emancipating and exhilarating and inadequate. Because, and I'm really not trying to be morose or emo or whatever here, because it seems like behind all of those attempts to connect, even the ones motivated by joy and virtue and the better things that fill our hearts, behind all of those attempts to connect is the desperate need to connect, the urge, and it seems like that urge can never be truly discharged. And even diagnosing that urge in yourself and sympathizing with it in others doesn't really close the gap. We can't even connect about our need to connect.
Here's a photo of the reader from W+K's 25th Anniversary book.